US4783475A - Compositions containing α-(1-cyclopropylethyl)-α-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol and a guanidine compound and fungicidal use thereof - Google Patents

Compositions containing α-(1-cyclopropylethyl)-α-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol and a guanidine compound and fungicidal use thereof Download PDF

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US4783475A
US4783475A US07/074,797 US7479787A US4783475A US 4783475 A US4783475 A US 4783475A US 7479787 A US7479787 A US 7479787A US 4783475 A US4783475 A US 4783475A
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formula
compound
acid addition
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Hans Wiedmer
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Sandoz AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof

Definitions

  • the present invention relates to fungicides.
  • the invention provides a method of combatting fungal diseases in plants, with the aid of
  • the compounds of formula I and II may be in free base form or in fungicidally acceptable acid addition salt form. Said salt forms exhibit the same order of activity as the free base forms.
  • the compound of the formula I (which may be named ⁇ -(1-cyclopropylethyl)- ⁇ -(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol) is a known fungicide, effective in the combatting of fungi in crops such as cereals including rice, especially in wheat and barley; it has excellent activity against rusts (such as Puccinia spp.), good activity against powdery mildews (such as Erysiphe), and interesting suppressive activities against Septoria, Pyrenophora, Rhynchosporium and Pseudocercosporella.
  • rusts such as Puccinia spp.
  • powdery mildews such as Erysiphe
  • the compound of formula I is usually employed in free base form.
  • the compound of formula II is known to be effective against plant fungi and used i.a. for cereal seed treatment and, in foliar spray form, against phytopathogenic fungi such as Pyricularia oryzae (in rice) and Septoria spp. (in wheat).
  • the triacetate salt of the compound of formula II is known under the common name iminoctadine. Said triacetate salt is also an active ingredient of the plant fungicidal mixture known under the common name guazatine.
  • the test results indicate that the combination of the invention is surprisingly effective against powdery mildews, foot diseases and ear diseases, and is accordingly particularly indicated for use in crops sensitive to such diseases.
  • crops comprise cereals (including including herein--by definition--rice) and vines, particularly wheat, barley and rice, more particularly wheat and barlry.
  • the invention provides an improved method of combatting fungal diseases in plants, especially in cereals, which comprises, applying to the plants, in admixture or separately, the compounds of the formulae I and II in free base form or agriculturally acceptable salt form, in a fungicidally effective aggregate amount.
  • the compounds are conveniently employed as foliar sprays.
  • Suitable weight ratios of the compound of formula I:iminoctadine lie in the range of 4:1 to 1:8, particularly of 3:1 to 1:6, more particularly of 3:1 to 1:4, most particularly of 2:1 to 1:4.
  • the experimental data given hereinafter show for example synergism for several crop/fungus diseases for the weight ratios 2:1, 1:1 and 1:2 (i.e. for the range 2:1 to 1:2).
  • the compound of formula II is in base form, or in a salt form other than the triacetate form it will in general be appropriate to adapt the amount of compound of formula II to be employed in the method and compositions of the invention by a factor equivalent to the molecular weight ratios of the base form or particular salt form to that of the triacetate salt form.
  • the amount of the compound of formula II to be applied when in base form would be a factor of about 0.66 lower, and be in the range of from 66 to 330 g, particularly from 132 to 264, e.g. 165.
  • weight ratios where, for example, both compounds are applied in base form the weight ratio of the compound of formula I:compound of formula II are conveniently in the range of 6:1 to 1:5.3, particularly of 4.5:1 to 1:2.6, moreparticularly of from 4.5:1 to 1:2.6, most particularly of from 3:1 to 1:2.6, e.g. of from 3:1 to 1:1.3.
  • the invention also provides fungicidal compositions comprising the compounds of formula I and II, preferably in a weight ratio within the range specified herein above.
  • compositions of the invention may be formulated in any conventional form, for example in the form of a twin packet, or of an emulsifiable concentrate, wettable powder or water dispersible granule.
  • Such compositions may be produced in conventional manner, e.g. by mixing the compounds of formula I and II with appropriate adjuvants such as diluents and optionally other formulating ingredients such as surfactants.
  • diluent as used herein means any liquid or solid agriculturally acceptable material--including carriers--which may be added to the active constituents to bring them in an application or commercial form, respectively, to a usable or desirable strength of activity. It can for example be talc, kaolin, diatomaceous earth, mineral oil, or water.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactants such as wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol.
  • surfactants such as wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% of diluent, the active agent consisting of the compounds of formula I and II and optionally other active agents.
  • compositions of the invention may comprise further additives with special purposes, such as anti-foaming agents.
  • further fungicides with similar or complementary fungicidal activity e.g. tridemorph, fenpropimorph, fenpropidin, pyrazophos, prochloraz, mancozeb, sulphur and carbendazim, or other beneficially-acting materials, such as insecticides may be present in the formulation.
  • compositions in general contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 45% by weight.
  • the compounds are mixed and milled until the mean particle size is about 5 microns.
  • Wheat is cultivated in a mixture of peat and sand in plastic pots of 6 cm diameter for x days.
  • the plants are sprayed with aqueous spray liquors containing the compound of formula I, iminoctadine or mixtures thereof (hereinafter a.i.) in various concentrations.
  • the treatment comprises foliar spraying to near run-off.
  • the plants are inoculated by dusting them with freshly collected conidia and are then incubated in an incubation chamber at 60-80% relative humitiy, 16 hours daylight and 20°-25° C.
  • the efficacy of the a.i. is determined by the degree of fungal attack with that on untreated, similarly inoculated check plants, and is expressed in % control for a given test concentration.
  • EC 90 exp. value i.e. the concentration of each a.i. allowing 90% disease control.
  • the experimental result (EC 90 exp.) for a given weight ratio of the compounds of formula I and iminoctadine is compared with the corresponding EC 90 theor. value, i.e. the concentration of that particular mixture allowing 90% disease control calculated according to Wadley ##EQU1## wherein a and b are the weight ratios of the compounds of formula I and iminoctadine resp.
  • indexes (I), (II) and (I+II) refer to the EC 90 values of the compound of formula I, iminoctadine and the a:b mixture of the compound of formula I with iminoctadine resp.
  • EC(I+II)90 theor. is greater than EC(I+II)90 exp., or the level or interaction, i.e. the synergy factor (SF) ##EQU2##

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a method of combatting fungal diseases with the aid of
(a) the compound of formula I ##STR1## and (b) the compound of formula II ##STR2## and fungicidal compositions comprising said compounds.

Description

The present invention relates to fungicides.
The invention provides a method of combatting fungal diseases in plants, with the aid of
(a) the compound of formula I ##STR3## and (b) the guanidine compound of formula II ##STR4##
The compounds of formula I and II may be in free base form or in fungicidally acceptable acid addition salt form. Said salt forms exhibit the same order of activity as the free base forms.
The compound of the formula I (which may be named α-(1-cyclopropylethyl)-α-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol) is a known fungicide, effective in the combatting of fungi in crops such as cereals including rice, especially in wheat and barley; it has excellent activity against rusts (such as Puccinia spp.), good activity against powdery mildews (such as Erysiphe), and interesting suppressive activities against Septoria, Pyrenophora, Rhynchosporium and Pseudocercosporella.
The compound of formula I is usually employed in free base form.
The compound of formula II is known to be effective against plant fungi and used i.a. for cereal seed treatment and, in foliar spray form, against phytopathogenic fungi such as Pyricularia oryzae (in rice) and Septoria spp. (in wheat). The triacetate salt of the compound of formula II is known under the common name iminoctadine. Said triacetate salt is also an active ingredient of the plant fungicidal mixture known under the common name guazatine.
It has now been found that the use of the compound of formula I in combination with the compound of formula II (combination of the invention) is surprisingly effective in the combatting of various fungi. Thus, more than additive effect is i.a. observed in tests against Erysiphe (barley, wheat), Pyrenophora, Septoria and Pseudocercosporella.
Though the efficacy of the combination of the invention will depend on the particular fungi (disease) to be combatted, the crop involved, the desired treatment (foliar, soil or seed treatment), the weight ratio of the compound of formula I: compound of formula II and other parameters, the test results indicate that the combination of the invention is surprisingly effective against powdery mildews, foot diseases and ear diseases, and is accordingly particularly indicated for use in crops sensitive to such diseases. Such crops comprise cereals (including including herein--by definition--rice) and vines, particularly wheat, barley and rice, more particularly wheat and barlry.
Accordingly, the invention provides an improved method of combatting fungal diseases in plants, especially in cereals, which comprises, applying to the plants, in admixture or separately, the compounds of the formulae I and II in free base form or agriculturally acceptable salt form, in a fungicidally effective aggregate amount.
For control of air-borne fungi, the compounds are conveniently employed as foliar sprays.
Where the compound of formula II is employed in triacetate form, i.e. as iminoctadine, satisfactory results may, in general, be obtained when applying 50 to 100 g, particularly 60 to 80 g of the compound of formula I and 100 to 500 g, particularly 200 to 400 g, e.g. 250 of iminoctadine per hectare of crop locus.
Suitable weight ratios of the compound of formula I:iminoctadine lie in the range of 4:1 to 1:8, particularly of 3:1 to 1:6, more particularly of 3:1 to 1:4, most particularly of 2:1 to 1:4. Thus the experimental data given hereinafter show for example synergism for several crop/fungus diseases for the weight ratios 2:1, 1:1 and 1:2 (i.e. for the range 2:1 to 1:2).
Where the compound of formula II is in base form, or in a salt form other than the triacetate form it will in general be appropriate to adapt the amount of compound of formula II to be employed in the method and compositions of the invention by a factor equivalent to the molecular weight ratios of the base form or particular salt form to that of the triacetate salt form.
A similar consideration applies also to the compound of formula I when employed in salt form.
Thus, for example, the amount of the compound of formula II to be applied when in base form would be a factor of about 0.66 lower, and be in the range of from 66 to 330 g, particularly from 132 to 264, e.g. 165.
Similar adaptation is appropriate with respect to the weight ratios; where, for example, both compounds are applied in base form the weight ratio of the compound of formula I:compound of formula II are conveniently in the range of 6:1 to 1:5.3, particularly of 4.5:1 to 1:2.6, moreparticularly of from 4.5:1 to 1:2.6, most particularly of from 3:1 to 1:2.6, e.g. of from 3:1 to 1:1.3.
The invention also provides fungicidal compositions comprising the compounds of formula I and II, preferably in a weight ratio within the range specified herein above.
Such compositions of the invention may be formulated in any conventional form, for example in the form of a twin packet, or of an emulsifiable concentrate, wettable powder or water dispersible granule. Such compositions may be produced in conventional manner, e.g. by mixing the compounds of formula I and II with appropriate adjuvants such as diluents and optionally other formulating ingredients such as surfactants.
The term diluent as used herein means any liquid or solid agriculturally acceptable material--including carriers--which may be added to the active constituents to bring them in an application or commercial form, respectively, to a usable or desirable strength of activity. It can for example be talc, kaolin, diatomaceous earth, mineral oil, or water.
Particularly formulations to be applied in spraying forms such as water dispersible concentrates or wettable powders may contain surfactants such as wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol.
In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% of diluent, the active agent consisting of the compounds of formula I and II and optionally other active agents.
In addition to the usual diluents and surfactants, the compositions of the invention may comprise further additives with special purposes, such as anti-foaming agents. Moreover, further fungicides with similar or complementary fungicidal activity, e.g. tridemorph, fenpropimorph, fenpropidin, pyrazophos, prochloraz, mancozeb, sulphur and carbendazim, or other beneficially-acting materials, such as insecticides may be present in the formulation.
Concrete forms of compositions in general contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 45% by weight.
The invention is illustrated by the following examples, wherein parts and percentages are by weight.
FORMULATION EXAMPLE 
______________________________________                                    
Wettable Powder    Parts                                                  
______________________________________                                    
Compound of formula I                                                     
                   40                                                     
Iminoctadine       40                                                     
Na dodecylsulphate  1                                                     
Na lignin sulphonate                                                      
                    5                                                     
Kaolin             14                                                     
______________________________________
The compounds are mixed and milled until the mean particle size is about 5 microns.
GREENHOUSE TEST In vivo employing Erysiphe graminis fs. tritici on wheat
Wheat is cultivated in a mixture of peat and sand in plastic pots of 6 cm diameter for x days. The plants are sprayed with aqueous spray liquors containing the compound of formula I, iminoctadine or mixtures thereof (hereinafter a.i.) in various concentrations. The treatment comprises foliar spraying to near run-off. After drying, the plants are inoculated by dusting them with freshly collected conidia and are then incubated in an incubation chamber at 60-80% relative humitiy, 16 hours daylight and 20°-25° C. The efficacy of the a.i. is determined by the degree of fungal attack with that on untreated, similarly inoculated check plants, and is expressed in % control for a given test concentration. Each a.i. is tested in different concentrations. This allows for the determination of the EC 90 exp. value, i.e. the concentration of each a.i. allowing 90% disease control. The experimental result (EC 90 exp.) for a given weight ratio of the compounds of formula I and iminoctadine is compared with the corresponding EC 90 theor. value, i.e. the concentration of that particular mixture allowing 90% disease control calculated according to Wadley ##EQU1## wherein a and b are the weight ratios of the compounds of formula I and iminoctadine resp. and the indexes (I), (II) and (I+II) refer to the EC 90 values of the compound of formula I, iminoctadine and the a:b mixture of the compound of formula I with iminoctadine resp. In the case of synergism EC(I+II)90 theor. is greater than EC(I+II)90 exp., or the level or interaction, i.e. the synergy factor (SF) ##EQU2##
Analogous tests are run with
Erys. gram. f. sp. hordei on barley
Pyrenophora on barley
Septoria on wheat, and
Pseudocercosporella on wheat
The results in which EC 90 values are expressed in ppm or mg/liter are as follows:
______________________________________                                    
                     EC90  EC90                                           
                     exp.  theor.  SF                                     
______________________________________                                    
1.  Erysiphe/barley                                                       
    Compound of formula I      3.1                                        
    Iminoctadine               37.0                                       
    Weight ratio of compounds of                                          
                       1.0:0.5 2.9   4.46  1.5                            
    formula I:iminoctadine                                                
                       1.0:1.0 2.8   5.72  2.0                            
                       1.0:2.0 3.2   7.97  2.5                            
2.  Erysiphe/wheat                                                        
    Compound of formula I      2.5                                        
    Iminoctadine               35.0                                       
    Weight ratio of compounds of                                          
                       1.0:0.5 2.9   3.62  1.3                            
    formula I:iminoctadine                                                
                       1.0:1.0 2.5   4.67  1.9                            
                       1.0:2.0 2.8   6.56  2.3                            
3.  Pyrenophora/barley                                                    
    Compound of formula I      11.00                                      
    Iminoctadine               18.00                                      
    Weight ratio of compounds of                                          
                       1.0:0.5 8.5   12.64 1.5                            
    formula I:iminoctadine                                                
                       1.0:1.0 6.3   13.66 2.2                            
                       1.0:2.0 5.8   14.85 2.6                            
4.  Septoria/wheat                                                        
    Compound of formula I      10.0                                       
    Iminoctadine               24.0                                       
    Weight ratio of compounds of                                          
                       1.0:0.5 3.2   12.41 3.9                            
    formula I:iminoctadine                                                
                       1.0:1.0 6.0   14.12 2.4                            
                       1.0:2.0 7.5   16.36 2.2                            
5.  Pseupocercosporella/wheat                                             
    Compound of formula I      32.0                                       
    Iminoctadine               29.0                                       
    Weight ratio of compounds of                                          
                       1.0:0.5 8.5   30.93 3.6                            
    formula I:iminoctadine                                                
                       1.0:1.0 9.0   30.43 3.4                            
                       1.0:2.0 11.0  29.94 2.7                            
______________________________________

Claims (12)

I claim:
1. A method of combatting a fungus disease selected from the group consisting of Erysiphe, Pyrenophora, Septoria and Pseudocercosporella in crop plants sensitive to such a fungus comprising applying to the plants in a crop locus, in admixture or separately, a fungicidal effective total amount of
(a) the compound of the formula I ##STR5## and (b) the compound of the formula II ##STR6## said compounds of the formulae I and II independently being in free base or acid addition salt form and the weight ratio of the compound of the formula I to the compound of the formula II in such application being in the range equivalent to 2:1 to 1:2 on the basis of the compound of the formula I in free base form and the compound of the formula II in triacetate acid addition salt form.
2. The method of claim 1, which comprises applying per hectare of crop locus from 50 to 100 g of the compound of formula I in base form or an equivalent amount of said compound in acid addition salt form, and from 100 to 500 g of the triacetate of the compound of formula II or an equivalent amount of said compound in another acid addition salt form or in base form.
3. The method of claim 1, wherein the crop is a cereal or vine crop.
4. The method of claim 3, in which Erysiphe graminis, Pyrenophora, Septoria or Pseudocercosporella spp is combatted in a cereal crop.
5. The method of claim 2 in which the compound of the formula I is applied in free base form and the compound of the formula II is applied in triacetate acid addition salt form.
6. The method of claim 5, wherein the applied amount per hectare of crop locus compound of formula I in base form is from 60 to 80 g and that of the compound of formula II in triacetate form is from 200 to 400 g.
7. The method of claim 3 in which Erysiphe is combatted in barley or wheat.
8. The method of claim 3 in which Pyrenophora is combatted in barley.
9. The method of claim 3 in which Septoria is combatted in wheat.
10. The method of claim 3 in which Pseupocercosporella is combatted in wheat.
11. A fungicidal composition comprising an agriculturally acceptable diluent and a fungicidally effective total amount of
(a) the compound of the formula I ##STR7## and (b) the compound of the formula II ##STR8## said compounds of the formula I and II independently being in free base or acid addition salt form and the weight ratio of the compound of the formula I to the compound of the formula II being in the range equivalent to 2:1 to 1:2 on the basis of the compound of the formula I in free base form and the compound of the formula II in triacetate acid addition salt form.
12. The composition of claim 11 in which the compound of the formula I is in free base form and the compound of the formula II is in triacetate acid addition salt form.
US07/074,797 1986-07-21 1987-07-17 Compositions containing α-(1-cyclopropylethyl)-α-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol and a guanidine compound and fungicidal use thereof Expired - Fee Related US4783475A (en)

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GB8617780 1986-07-21
GB868617780A GB8617780D0 (en) 1986-07-21 1986-07-21 Fungicides

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166058A (en) * 1996-07-10 2000-12-26 Basf Aktiengesellschaft Fungicidal mixtures

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3800094C2 (en) * 1987-01-14 1998-05-14 Ciba Geigy Ag Process and hydrophobic preparation for combating cut parasites in plants
DE4203090A1 (en) * 1992-02-04 1993-08-19 Hoechst Holland Nv SYNERGISTIC COMBINATIONS OF CYPROCONAZOLE
DE4231073A1 (en) 1992-09-17 1994-03-24 Rhein Chemie Rheinau Gmbh Phosphorylation of epoxides
JP4830248B2 (en) * 2001-09-27 2011-12-07 住友化学株式会社 Disinfectant composition and crop disease control method
CN102090414B (en) * 2010-12-27 2013-07-31 江苏龙灯化学有限公司 Bactericide composition with synergized action
CN102715181B (en) * 2012-06-05 2014-05-07 江苏龙灯化学有限公司 Sterilization composition with synergetic effect
CN102687725B (en) * 2012-06-05 2014-01-01 江苏龙灯化学有限公司 Bactericidal composition containing active components of bellkute and thiabendazole
WO2014092865A2 (en) 2012-12-10 2014-06-19 Milliken & Company Cleaning composition and method for using the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3499927A (en) * 1964-08-24 1970-03-10 Evans Medical Ltd Guanidino derivatives of polyalkylene polyamines
GB2064520A (en) * 1979-11-13 1981-06-17 Sandoz Ltd alpha -Amyl-1H-1,2,4-triazole-1- ethanols
EP0155509A1 (en) * 1984-02-24 1985-09-25 Dainippon Ink And Chemicals, Inc. Agricultural and horticultural guanidine-type fungicide and process for production thereof
US4664696A (en) * 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3499927A (en) * 1964-08-24 1970-03-10 Evans Medical Ltd Guanidino derivatives of polyalkylene polyamines
US3639631A (en) * 1964-08-24 1972-02-01 Evans Medical Ltd Method of controlling fungi and bacteria
GB2064520A (en) * 1979-11-13 1981-06-17 Sandoz Ltd alpha -Amyl-1H-1,2,4-triazole-1- ethanols
US4664696A (en) * 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus
EP0155509A1 (en) * 1984-02-24 1985-09-25 Dainippon Ink And Chemicals, Inc. Agricultural and horticultural guanidine-type fungicide and process for production thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166058A (en) * 1996-07-10 2000-12-26 Basf Aktiengesellschaft Fungicidal mixtures

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DE3764739D1 (en) 1990-10-11
ATE56122T1 (en) 1990-09-15
AU596436B2 (en) 1990-05-03
AU7591187A (en) 1988-01-28
JPS6333309A (en) 1988-02-13
PT85358B (en) 1989-10-16
KR880001618A (en) 1988-04-25
EP0255987A1 (en) 1988-02-17
MY102506A (en) 1992-07-31
PT85358A (en) 1987-08-01
DK377687D0 (en) 1987-07-20
GB8617780D0 (en) 1986-08-28
BR8703761A (en) 1988-03-29
ZA875355B (en) 1989-03-29
EP0255987B1 (en) 1990-09-05
DK377687A (en) 1988-01-22
HUT47396A (en) 1989-03-28

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